Courtesy: REGENCY REAL ESTATE LLC
407-469-5021
Stunning J&J Model Home in Briley Farm – Leaseback Opportunity! Step into unmatched luxury at this impeccably crafted J&J Building model home, perfectly positioned on a premier corner lot in the sought-after Briley Farm community of Oakland, FL. Designed with exceptional attention to detail, this residence offers 4 bedrooms, 4 full baths, 2 powder baths, a loft, bonus room, private office, two laundry rooms, and a detached casita with a full ensuite—ideal for guests, in-laws, or extended stays. Inside, the home showcases elevated finishes at every turn, including Sierra Pacific windows—62 in total—filling the home with natural light, an impressive Euro-style 9'+ bifold slider, and a stunning gas fireplace anchoring the main living space. The chef’s kitchen boasts Wolf and Sub-Zero appliances, exquisite Quartzite counters in both the main and back kitchens, and a fully equipped back kitchen designed for effortless entertaining. A custom primary closet with lighted rods adds a boutique touch to everyday living. Outdoor living is equally exceptional. Enjoy a lap pool and hot tub, gas fire pit, and luxurious marble coping and pool decking, all beautifully framed by a $70,000 professionally designed landscaping package and a fully fenced yard for privacy. Additional upgrades include Sonos speakers, security system with cameras, clay tumbled pavers on the porches, and a Generac generator for added comfort and peace of mind. With a 4-car garage, impeccable craftsmanship, and a leaseback opportunity, this home offers the best of luxury and convenience. Furniture is negotiable, allowing you to tailor the space to your vision. Discover refined living in one of Oakland’s most desirable communities—this model home truly sets the standard.
Courtesy: OAKSTRAND REALTY
888-912-5258
This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant woodworking, tall windows, 10’ ceilings, and elegant staircases. French doors connect the formal dining and living room to a grand Florida room with a hot tub and outdoor porch. A modern island kitchen features stainless steel appliances, 3 sinks, and a large pantry. A luxury updated master suite with a soaking tub is on the first floor, along with a private apartment with its own kitchen and separate entrance. The 2nd floor offers 4 themed bedroom suites, an upstairs living room/ lounge, and a porch with views of Lake Apopka. All rooms have an internet-based locking system. The Oakland Manor House is conveniently located within 30 minutes of downtown Orlando, Disney, and Universal Studios. The West Orange Trail runs through the neighborhood. Easy biking distance to Winter Garden, which offers restaurants, farmer’s market, brewery, and music venues. The Oakland Nature Preserve is another nearby treasure. This is a unique opportunity to own a part of Oakland's history. Bring your business ideas or reside in your own retreat. The sky is the limit!
Courtesy: CORCORAN PREMIER REALTY
407-965-1155
Under Construction. Introducing an extraordinary luxury estate by Element Home Builders in the sought after Briley Farm community, where timeless design, exceptional craftsmanship, and modern elegance come together on a beautiful oversized, nearly half acre corner lot. This remarkable 6-bedroom, 6.5-bath custom residence offers an unparalleled living experience with every detail thoughtfully curated for comfort, sophistication, and style. From the moment you arrive, the home commands attention with its architectural presence and grand entryway. Inside, soaring ceilings, designer finishes, and expansive living spaces create a refined yet inviting atmosphere. The heart of the home is the gourmet chef’s kitchen, seamlessly connected to the main living areas and perfect for both intimate gatherings and large-scale entertaining. A private office provides the ideal work-from-home environment, while multiple ensuite bedrooms ensure comfort and privacy for family and guests. The 4-car garage offers ample space for vehicles, storage, or a future car collection. Resort-style outdoor living takes center stage with a beautifully appointed summer kitchen, covered lanai, and a sparkling custom pool with spa, all overlooking the lush, manicured grounds of the corner lot. Whether hosting celebrations or enjoying quiet evenings at home, this outdoor oasis elevates everyday living. Nestled within one of Oakland’s most coveted luxury communities- Briley Farm, this home offers exclusivity, elegance, and convenience—just minutes from vibrant Winter Garden, top-rated schools, charming parks, and premier dining. A true masterpiece in Briley Farm, this residence delivers the ultimate blend of luxury and lifestyle.
Courtesy: REAL BROKER, LLC
855-450-0442
One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 507 W Oakland Avenue, where comfort, charm, and convenience come together in one perfect location! Nestled in the heart of Oakland, this beautiful home offers one of the most desirable addresses in the area. Enjoy being just steps from the neighborhood park, a mile from the scenic Oakland Orange Bike Trail and City Hall, only 5 minutes from vibrant Downtown Winter Garden, and a quick 30-minute drive to the magic of Disney World. You’ll love living close to shopping, dining, and entertainment while still enjoying the peaceful small-town feel. Move-in ready and beautifully maintained, this home features 3 spacious bedrooms and 2 full bathrooms. The open and inviting floor plan offers a bright living room filled with natural light, a cozy family room ideal for relaxing, and a large dining area that’s perfect for hosting gatherings. The welcoming foyer greets you with a flexible space that can be used as a home office, reading nook, or a stylish sitting area. The kitchen boasts ample cabinet space, modern appliances, and a breakfast bar for casual dining. Additional highlights include: Central air conditioning and heating throughout the home Ceiling fans with lighting in each bedroom Freshly painted interiors with neutral tones Brand new Laminate wood-style flooring for easy maintenance Indoor laundry area for added convenience Fully fenced yard offering privacy and security Gated driveway with plenty of parking space Spacious backyard perfect for pets, play, or outdoor entertaining Whether you’re looking for your first home, a family retreat, or a peaceful escape close to everything, 507 W Oakland Avenue is the perfect choice. Don’t miss out on this rare gem — call today to schedule your private tour and experience the charm of Oakland living!
Courtesy: BHHS FLORIDA REALTY
407-876-2090
Seller is offering First Mortgage Owner Financing up to $750,000 at 4.3% interest rate with a 3-year Balloon structure, to be organized by a real estate attorney. Welcome to 101 N Starr Street, an exceptional single-story, custom-built residence nestled in the heart of historic Oakland, Florida—where timeless craftsmanship, luxurious finishes, and everyday convenience blend effortlessly. Set beneath a canopy of majestic, centuries-old oaks, this meticulously designed home offers a rare combination of elegance, comfort, and accessibility. With a spacious open floor plan, soaring 14-foot ceilings, and oversized 8-foot doors throughout, the home is both grand in scale and thoughtfully functional. Fully handicap accessible and designed with mobility in mind, it offers seamless, barrier-free living that accommodates all stages of life. At the heart of the home lies a gourmet kitchen, professionally designed by a chef and custom builder. This culinary centerpiece features top-of-the-line appliances, generous prep space, and luxury finishes—perfect for everything from everyday meals to large-scale entertaining. The open-concept design continues into expansive living and dining areas that flow effortlessly into the outdoors, creating an ideal environment for both intimate gatherings and lively celebrations. Step outside to your own private oasis: a beautifully screened-in pool, complemented by a fully equipped summer kitchen and ample patio space for lounging or dining under the stars. Whether you’re enjoying a quiet morning coffee poolside or hosting a weekend cookout, the outdoor living area is designed to elevate your lifestyle year-round. Located just steps from the Oakland Farmers Market, Charter School, Heritage Center, and Post Office, this home is at the center of a walkable, welcoming community where neighbors know one another and nature thrives. With direct golf cart access to vibrant Downtown Winter Garden, you’re only minutes from award-winning restaurants, unique shops, live entertainment, and a bustling weekly farmers market. Outdoor enthusiasts will love the nearby West Orange Trail and Lake Apopka’s scenic shoreline, perfect for biking, walking, birdwatching, or kayaking. And when adventure calls, you’re a short drive from some of the world’s most celebrated destinations, including Walt Disney World, Universal Studios, and Downtown Orlando. Combining small-town charm with big-city convenience, this location is truly second to none. More than just a residence, 101 N Starr Street is a destination for those seeking refined, accessible living in one of Central Florida’s most desirable communities. With its custom design, premium features, and unbeatable location, this home offers a lifestyle of beauty, comfort, and lasting value.
Oakland is located in Florida. Oakland, Florida 34760has a population of 3,444. Oakland 34760 is more family-centric than the surrounding county with 42.93% of the households containing married families with children. The county average for households married with children is 31.51%.
The median household income in Oakland, Florida 34760 is $124,856. The median household income for the surrounding county is $65,784 compared to the national median of $69,021. The median age of people living in Oakland 34760 is 37.1 years.
The average high temperature in July is 92.2 degrees, with an average low temperature in January of 46.8 degrees. The average rainfall is approximately 52.1 inches per year, with 0 inches of snow per year.
